Honey, you can’t make it to the top without at some point scraping the cold, hard bottom. For the Portland Trail Blazers, their highest high (not a pun) came during the 1999-2000 NBA season, which they rode all the way to the Western Conference finals for the second year in a row, and almost made it to the very end. But after nearly winning game seven by 15 before losing their mojo and seeing their dreams stomped out by a Shaq and Kobe-led Lakers, they notoriously tumbled into a dark hollow that would plague them.

This was the era of the Portland “Jail Blazers,” and to some, it was a despicable epoch. To me, though, that time was audacious, glorious. (Not least because I lived there at the time, and they eventually became so reviled that the Rose Garden was practically paying us to attend the games. You could get decent seats for, like, 10 bucks!) It was also a distillation of one of the worst parts of America, when an almost entirely white city (statistically the whitest city in America, it turns out) turned against a team almost the moment it fell off its winning streak, eventually reviling them as arrogant rule-breakers—which no doubt made them more defiant and prone to breaking the rules.

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Though it’s now so emblematic of a certain type of artisanal culture that it’s been spoofed for several seasons on IFC’s Portlandia, Portland at the turn of the millennium was a small city with a somewhat provincial feel, a community-oriented town just learning how to grow, even a little bit, into what it has become. It was then and is surely now a city with fairly progressive politics, and those politics often encompass marijuana. Obviously, weed and vibes brings tons of hippies to its ranks, but there’s also the fact that virtually everybody loves weed. (A very stupid joke, when our team would play Denver, was “BLAZERS VERSUS NUGS,” WINK WINK. Do people still do that? So dumb, but I loved it.)

The weed lovers, of course, included the Trailblazers who, as you can surmise, became the “Jail Blazers” because some of them—the gods Rasheed Wallace and Damon Stoudamire in particular—had some unfortunate encounters with the law. And some of the most notable of these encounters involved marijuana.

Obviously, there was a major racial element to this—in a city of relatively few black people, the Portland Police have been accused of racial profiling as much as any other department, and in a city of relatively modest values, certainly rich NBA players tooling around town attracted attention. (Sidebar: if you have never seen the Rasheed Wallace episode of Cribs, I suggest you do so immediately.)

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Back then, the Blazers had many excellent individual players who had a tough time finding the right kind of synergy to be a team. They had a good but—with this group—frustratingly ineffective coach in Mo Cheeks. Then factor in Wallace as a team leader (great player with an ineffable temper), and the whole thing was incredibly volatile. And yet despite all of it, they were still winning, which no doubt led to their frustration—that a city would abandon its team because of a moral judgment rather than shitty games.

On the other hand, some of the shit Blazers team members did to get in trouble was inexcusably dumb. Consider what is probably the most tragic (and, conceptually, my favorite) incident: On November 21, 2002, the Blazers had just defeated the Seattle SuperSonics (RIP!!), and Wallace, Stoudemire and a friend were driving back to Portland down Interstate 5.

Unfortunately for them, they were driving Stoudemire’s banana yellow Hummer H2—not exactly the most inconspicuous vehicle, particularly in a region where environmental activists torching SUV dealerships was NBD—while doing 84 in a 70, which caused a highway patrol to pull them over for speeding. When he did so, the cop noticed that they were smoking weed. They were cited for misdemeanor possession, and Wallace publicly apologized to his wife, children, coach, and teammates. “We don’t want to be a distraction for Blazers basketball as far as a players’ standpoint or a fans’ standpoint,” he said.

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By the end of 2003, though, a total of four Blazers had been in trouble for weed possession—Wallace, Stoudemire (thrice, including one dumb time when he tried to carry it on a plane?? In Arizona???), Qyntel Woods (we’ll come back to him later) and, in the most devastating incident, the beloved young Z-Bo, Zach Randolph. The 22-year-old rookie got busted for smoking weed while driving his Cadillac.

That incident coincided with the moment that General Manager John Nash (god, I loathed John Nash) traded Bonzi Wells (god, I loved Bonzi Wells) to the Grizzlies for Wes Person, whose time on the team I barely remember but who apparently was greeted with joy:

When Person checked into the game against the Knicks in the first quarter Friday night, the fans cheered mightily for more than a minute.

The Blazers fined Wells $10,000 last month for making an obscene gesture to fans, and suspended him for two games for cursing at Cheeks on the sideline. Cheeks had stripped Wells of the captaincy he had given him this season to make him more responsible after three years of insubordinate incidents.

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It’s true that Portland sentiment turned quickly against Wallace (who incurred so many infractions on the court it was almost a job hazard just to play with him, opponent or no) and especially Wells, who in 2002 famously toldSports Illustrated:

“We’re not really going to worry about what the hell [the fans] think about us. They really don’t matter to us. They can boo us every day, but they’re still going to ask for our autographs if they see us on the street. That’s why they’re fans and we’re NBA players.”

Sure, that quote can be seen as a symbol of the outsized cockiness that scourged the NBA at the time, but in the context of the way the players were being treated by fans, in Portland, a town where white liberalism has its limits, I can also see the other side. The crowds were thinning, and sentiment was hostile. For a weedy city, lambasting players for getting caught smoking was both hypocritical and racial. At a certain point, the players’ inherent audacity combined with defiance at the way they were treated.

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Fifteen years later, weed is finally legal in Oregon, and in the last few years the Blazers have been somewhere between good and great. Is that a coincidence? Probably, but it’s definitely not a coincidence that its team hasn’t had these struggles since contracts ran out and the “Jail Blazers” dissipated. It’s wild to imagine that time, when Paul Allen owned Portland’s only national sports team as well as its only rap station (Jammin 95.5, which unfortunately later became a sports station), and when all a lot of great players really needed was to be rearranged, put on a different team and in a different environment to thrive.

‘Sheed, who left in 2004, ended up on the Pistons after a short stint with the Hawks, and led Detroit to victory in a beautiful series I still hold dear to my heart. (Not least because I watched the championship-clinching game with a good friend and a whole bunch of random dudes buying pitchers at the Times Square ESPN Zone. RIP, ESPN Zone.) Chauncey Billups was the MVP, but he couldn’t have done it without Sheed, who in a way brought it all full circle by murking Shaq and Kobe’s Lakers. It was the ultimate bird to a city that didn’t seem to want him.